CN103265461B - A kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt and preparation method thereof - Google Patents
A kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt and preparation method thereof Download PDFInfo
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- CN103265461B CN103265461B CN201310233013.9A CN201310233013A CN103265461B CN 103265461 B CN103265461 B CN 103265461B CN 201310233013 A CN201310233013 A CN 201310233013A CN 103265461 B CN103265461 B CN 103265461B
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Abstract
The present invention relates to a kind of preparation method of new nonionic surfactant alkyl (sulfophenoxy) Phenylsulfonic acid disalt, be specially: with halogeno-benzene and alkylphenol for main raw material, under acid binding agent and mantoquita exist, etherificate under 80-180 DEG C of temperature condition, generate intermediates alkyl phenoxy benzene and by-product halogen, filtering copper salt catalyst and by-product halogen, heat up in a steamer except halogeno-benzene at 85-200 DEG C, and then add inert organic solvents and sulphonating agent 0-80 DEG C of sulfonation in the presence of an organic, generate alkyl (sulfophenoxy) Phenylsulfonic acid, add alkaline neutraliser and neutralize pH value 6.5-7.5, generate alkyl (sulfophenoxy) Phenylsulfonic acid disalt.
Description
Technical field the invention belongs to chemical and manufactures field, is specifically related to a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt and preparation method thereof.
Background technology
Alkyl (sulfophenoxy) Phenylsulfonic acid disalt is the tensio-active agent of an excellent cost performance, the whole dependence on import of these series product that current domestic enterprise uses, and the domestic composition problem that there is no actual this product of solution, also appears on the market without homemade goods.I, by the effort more than 1 year, addresses this problem, and the actual finished product synthesizing excellent result.Through comparing with external imported product, surface tension when concentration 0.1%, all in 29-31 dynes per centimeter, can import substitutes completely.Product has extensive use at industrial circles such as oil production, textile printing and dyeing, latex processing;
In product synthesis, at present, domesticly there is no substantive launch products, illustrate that domestic enterprise also exists a little difficulty in this technical field, external mainly employing with phenyl ether as Dow Chemical company is substrate, the processing method synthetic mesophase product alkyl phenoxy benzene being alkylating reagent with poly-tetrapropylene, but the said firm's product after testing two alkyl ratio reaches 10-20%, affect quality product, be mainly reflected in the impact of effects on surface tension force large, the present invention adopts the technique of sulfonation again after monoalkyl phenol and halogeno-benzene etherificate, avoid the generation of two alkyl, achieve desirable effect, the excellent 20-30% of product surface warp tension ratio import like product, and raw material is easy to get, with low cost, especially bromobenzene is used, phenyl-iodide, when fluorobenzene is raw materials technology, gained by-product halogen also can obtain fabulous economic benefit after recrystallizing and refining, and avoid a large amount of Industrial Salt need phenomenon to be processed of generation, very favourable to environment protection, it is a kind of very good synthetic method.
Summary of the invention
Goal of the invention: problem to be solved by this invention is to provide a kind of anion surfactant replacing import like product, a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt and preparation method thereof;
The present invention realizes goal of the invention especially by following steps:
(1) in the etherifying reactor that reflux is housed, add 1-10mol halogeno-benzene and 1-10mol alkylphenol alkylphenol be alkyl C number be 3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18 alkylphenol, the alkyl of this alkylphenol can be at the contraposition of hydroxyl, a position or ortho position, can be normal chain alkyl or isomery alkyl;
(2) then add acid binding agent to above-mentioned etherifying reactor, and be filled with nitrogen protection, open and stir, be warming up to 85-200 DEG C, backflow, utilize halogeno-benzene band water point to anhydrate in water trap point, halogeno-benzene passes back into still, until purify moisture;
(3) drop into copper salt catalyst to etherification kettle, need nitrogen protection simultaneously, under 85-200 DEG C of temperature condition, insulation 1-5 hour, generates intermediates alkyl phenoxy benzene and by-product halogen;
(4) above-mentioned (3) product is filtered, filtering halogen and catalyzer;
(5) above-mentioned (4) filtrate, in 85-200 DEG C of underpressure distillation or rectifying, is sloughed excessive halogeno-benzene, obtain alkyl phenoxy benzene;
(6) above-mentioned (5) product alkyl phenoxy benzene is sent into sulfonation reaction still, and add inert organic solvents;
(7) add 1-10mol sulphonating agent to sulfonation reaction still, temperature control is 0-80 DEG C of sulfonation, and reaction 1-5 hour, generates alkyl (sulfophenoxy) Phenylsulfonic acid;
(8) in above-mentioned (7) sulfonated liquid, add water 10-60%, stir, then static acid out, removes spent acid layer after layering, and oil reservoir is the mixture of alkyl (sulfophenoxy) Phenylsulfonic acid and inert organic solvents;
(9) above-mentioned (8) product 20-100 DEG C underpressure distillation is removed inert organic solvents, obtain alkyl (sulfophenoxy) Phenylsulfonic acid;
(10) add water to above-mentioned (9) gained alkyl (sulfophenoxy) Phenylsulfonic acid and add alkaline neutraliser 1-3mol and be neutralized to the mixture that pH value 6.5-7.5 obtains alkyl (sulfophenoxy) Phenylsulfonic acid disalt and a small amount of insolubles;
(11) above-mentioned (10) gained material is filtered, filtering insolubles, to filtrate thin up to desired content, obtain light yellow finished product alkyl (sulfophenoxy) Phenylsulfonic acid two product salt;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, main raw material is: halogeno-benzene, alkylphenol, acid binding agent, sulphonating agent, alkaline neutraliser;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, synthesis material halogeno-benzene: alkylphenol: acid binding agent: sulphonating agent: the molar ratio of alkaline neutraliser is 1-10: 1-10: 1-10:1-10: 1-3;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, raw material
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, starting halo benzene is chlorobenzene, bromobenzene, iodobenzene, fluorobenzene;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, raw material acid binding agent can be sodium carbonate, salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, raw material sulphonating agent can be sulfuric acid, chlorsulfonic acid, thionamic acid, sulphur trioxide;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, raw material alkaline neutraliser is mineral alkali: sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate, lime etc. and organic amine series organic bases: trolamine, diethanolamine, thanomin, ammoniacal liquor, Monomethylamine, dimethylamine, Trimethylamine 99 etc.;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, catalyzer is the catalyzer of mantoquita series, can be the oxide compound of the hydrosulfate of copper, copper chloride, copper, and ingredient proportion is the 1-10% of halogeno-benzene and alkylphenol total amount;
The preparation of described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, inert organic solvents can be trichloromethane, methylene dichloride, 1,2-ethylene dichloride, 1,1,2,2 ,-tetrachloroethane, Nitromethane 99Min., trieline, tetracol phenixin, o-nitroethylbenzene, oil of mirbane, nitrotoluene, orthodichlorobenzene, sherwood oil, consumption is the 1-200% of material total amount;
Described a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt, in finished product structure, sulfonic group can be any position on phenyl ring;
A kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt as above, finished product is pH value scope at the oyster of 6.5-7.5 or light yellow liquid;
Effect of the present invention and benefit are:
(1) in synthetic technology: adopt etherificate route synthesis of alkyl phenoxy group benzene, avoid the generation of the by products such as polyalkylbenzene oxygen base benzene, make product performance be improved significantly, and technique is easily controlled;
(2) in economic benefit: the like product that instead of a large amount of import, decrease the interests loss of national industry, and become convenient due to buying after domesticizing, improve production and operation mode;
(3) in product performance: this excellent product performance, both had resistance to strong acid, highly basic, the properties such as inorganic salt, surface tension, when concentration 0.1%, can reach 29-31 dynes per centimeter, and has remarkable emulsifying property, and cheap, and cost performance is excellent.Product also alternative commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, alkyl sodium sulfonate, fatty alcohol-polyoxyethylene ether in the industrial circles such as oil production, textile printing and dyeing, latex processing, intermetallic composite coating, surface cleaning.In emulsification, dispersing property, acid-and base-resisting, inorganic salt, high-temperature behavior, be that current commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, fatty alcohol-polyoxyethylene ether etc. are wetting, dispersion, emulsified tensio-active agent 2-10 doubly.While increasing substantially product stability in use and effect, considerably reducing usage quantity, reduce use cost, reducing the environmental pollution indexes because using tensio-active agent to cause simultaneously;
Embodiment
Below by embodiment, illustrate the present invention further, this embodiment is only the present invention is described and never limits the present invention
Embodiment 1
Bromobenzene about 500 grams and dodecyl phenol about 262 grams is added in the reactor that reflux is housed, add solid sodium hydroxide about 30 grams, add solid potassium hydroxide about 21 grams, heated for controlling temperature is stirred at 30-50 DEG C the solid alkali added and all dissolves, add cuprous chloride about 15 grams, heat up, and open nitrogen protection, under 85-200 DEG C of temperature condition, insulation 1-5 hour, utilize the backflow of bromobenzene to be separated simultaneously and generate water, reaction reacts completely as terminal with dodecyl phenol, after terminal arrives, filtration catalizer cuprous chloride and Sodium Bromide, decompression is heated up in a steamer and is got unnecessary excessive bromobenzene, obtain dodecyl phenoxy group benzene, then sherwood oil 100 grams is added and the mixed solution started to sherwood oil and dodecyl phenoxy group benzene drips 120 oleum 200 grams, temperature control is at 0-80 DEG C, finish reaction 1-5 hour, survey terminal, after terminal arrives, sherwood oil is extracted in decompression, then about 200 grams are added water, stir half an hour, static, be separated residual acid after layering after, obtain dodecyl (sulfophenoxy) Phenylsulfonic acid, add water liquid caustic soda and a small amount of limestone vegetation to 6.5-7.5, filter, filtrate moisturizing is to finished product content about 45%, obtain dodecyl (sulfophenoxy) benzenesulfonic acid disodium salt finished product about 1000 grams, in dodecyl phenol, yield reaches more than 99%,
Embodiment 2
Bromobenzene about 500 grams and octyl phenol about 113 grams is added in the reactor that reflux is housed, add solid sodium hydroxide about 30 grams, add solid potassium hydroxide about 21 grams, heated for controlling temperature is stirred at 30-50 DEG C the solid alkali added and all dissolves, add cuprous chloride about 15 grams, heat up, and open nitrogen protection, under 85-200 DEG C of temperature condition, insulation 1-5 hour, utilize the backflow of bromobenzene to be separated simultaneously and generate water, reaction reacts completely as terminal with octyl phenol, after terminal arrives, filtration catalizer cuprous chloride and Sodium Bromide, decompression is heated up in a steamer and is got unnecessary excessive bromobenzene, obtain octyl phenoxy group benzene, then sherwood oil 100 grams is added and the mixed solution started to sherwood oil and octyl phenoxy group benzene drips 120 oleum 200 grams, temperature control is at 0-80 DEG C, finish reaction 1-5 hour, survey terminal, after terminal arrives, sherwood oil is extracted in decompression, then about 200 grams are added water, stir half an hour, static, be separated residual acid after layering after, obtain octyl (sulfophenoxy) Phenylsulfonic acid, add water and add trolamine and be neutralized to 6.5-7.5, filter, filtrate moisturizing is to finished product content about 45%, obtain octyl (sulfophenoxy) Phenylsulfonic acid two triethanolamine salt finished product about 1400 grams, in octyl phenol, yield reaches more than 99%,
Embodiment 3
Iodobenzene about 500 grams and octadecylphenol about 347 grams is added in the reactor that reflux is housed, add solid sodium hydroxide about 30 grams, add solid potassium hydroxide about 21 grams, heated for controlling temperature is stirred at 30-50 DEG C the solid alkali added and all dissolves, add cuprous chloride about 25 grams, heat up, and open nitrogen protection, because iodobenzene reactivity is stronger, need slow temperature control under 85-200 DEG C of temperature condition, insulation 1-5 hour, utilize the backflow of iodobenzene to be separated simultaneously and generate water, survey terminal, after terminal arrives, filtration catalizer cuprous chloride and sodium iodide, decompression is heated up in a steamer and is got unnecessary excessive iodobenzene, then methylene dichloride 100 grams is added and the mixed solution started to methylene dichloride and octadecyl phenoxy group benzene drips 232 grams of chlorsulfonic acids, temperature control is at 0-80 DEG C, finish reaction 1-5 hour, and the hydrogenchloride that tiny structure extracting simultaneously produces, reaction reacts completely as terminal with octadecylphenol, after terminal arrives, methylene dichloride is extracted in decompression, then about 200 grams are added water, stir half an hour, static, be separated residual acid after layering after, obtain octadecyl (sulfophenoxy) Phenylsulfonic acid, add water liquid caustic soda and a small amount of limestone vegetation to 6.5-7.5, filter, filtrate moisturizing is to finished product content about 45%, obtain octadecyl (sulfophenoxy) benzenesulfonic acid disodium salt finished product about 1200 grams, in octadecylphenol, yield reaches more than 99%.
Claims (9)
1. a preparation method for alkyl (sulfophenoxy) Phenylsulfonic acid disalt, it is characterized in that, building-up process comprises the steps and processing condition:
(1) in the etherifying reactor that reflux is housed, 1-10mol halogeno-benzene and 1-10mol alkylphenol is added, alkylphenol to be alkyl C number be 7,8,9,10,11,12,13,14,15,16,17,18 alkylphenol, the alkyl of this alkylphenol is at the contraposition of hydroxyl, a position or ortho position, be normal chain alkyl or isomery alkyl, described halogeno-benzene is chlorobenzene, bromobenzene, iodobenzene, fluorobenzene;
(2) then add acid binding agent to above-mentioned etherifying reactor, and be filled with nitrogen protection, open and stir, be warming up to 85-200 DEG C, backflow, utilize halogeno-benzene band water point to anhydrate in water trap point, halogeno-benzene passes back into still, until purify moisture;
(3) copper salt catalyst is dropped into etherification kettle, need nitrogen protection simultaneously, under 85-200 DEG C of temperature condition, insulation 1-5 hour, generate intermediates alkyl phenoxy benzene and by-product halogen, described catalyzer is the catalyzer of mantoquita series, is the oxide compound of the hydrosulfate of copper, copper chloride, copper, and ingredient proportion is the 1-10% of halogeno-benzene and alkylphenol total amount;
(4) above-mentioned (3) product is filtered, filtering halogen and catalyzer;
(5) above-mentioned (4) filtrate, in 85-200 DEG C of underpressure distillation or rectifying, is sloughed excessive halogeno-benzene, obtain alkyl phenoxy benzene;
(6) above-mentioned (5) product alkyl phenoxy benzene is sent into sulfonation reaction still, and add inert organic solvents;
(7) add 1-10mol sulphonating agent to sulfonation reaction still, temperature control is 0-80 DEG C of sulfonation, and reaction 1-5 hour, generates alkyl (sulfophenoxy) Phenylsulfonic acid;
(8) in above-mentioned (7) sulfonated liquid, add water 10-60%, stir, then static acid out, removes spent acid layer after layering, and oil reservoir is the mixture of alkyl (sulfophenoxy) Phenylsulfonic acid and inert organic solvents;
(9) above-mentioned (8) product 20-100 DEG C underpressure distillation is removed inert organic solvents, obtain alkyl (sulfophenoxy) Phenylsulfonic acid;
(10) add water to above-mentioned (9) gained alkyl (sulfophenoxy) Phenylsulfonic acid and add alkaline neutraliser 1-3mol and be neutralized to the mixture that pH value 6.5-7.5 obtains alkyl (sulfophenoxy) Phenylsulfonic acid disalt and a small amount of insolubles;
(11) above-mentioned (10) gained material is filtered, filtering insolubles, to filtrate thin up to desired content, obtain light yellow finished product alkyl (sulfophenoxy) Phenylsulfonic acid two product salt.
2. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, is characterized in that main raw material is: halogeno-benzene, alkylphenol, acid binding agent, sulphonating agent, alkaline neutraliser.
3. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1 is characterized in that: synthesis material halogeno-benzene: alkylphenol: acid binding agent: sulphonating agent: the molar ratio of alkaline neutraliser is 1-10: 1-10: 1-10:1-10: 1-3.
4. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, is characterized in that: described acid binding agent is sodium carbonate, salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide.
5. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, is characterized in that: described sulphonating agent is sulfuric acid, chlorsulfonic acid, thionamic acid, sulphur trioxide.
6. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, is characterized in that: described alkaline neutraliser is mineral alkali: sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate, lime and organic amine series organic bases: trolamine, diethanolamine, thanomin, ammoniacal liquor, Monomethylamine, dimethylamine, Trimethylamine 99.
7. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, it is characterized in that described inert organic solvents is trichloromethane, methylene dichloride, 1,2-ethylene dichloride, 1,1,2,2 ,-tetrachloroethane, Nitromethane 99Min., trieline, tetracol phenixin, o-nitroethylbenzene, oil of mirbane, nitrotoluene, orthodichlorobenzene, sherwood oil, consumption is the 1-200% of material total amount.
8. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1 is characterized in that: in finished product structure, sulfonic group is any position on phenyl ring.
9. the preparation method of a kind of alkyl (sulfophenoxy) Phenylsulfonic acid disalt according to claim 1, is characterized in that: finished product is pH value scope at the oyster of 6.5-7.5 or light yellow liquid.
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| US4959490A (en) * | 1988-11-14 | 1990-09-25 | Exxon Production Research Company | Process for manufacturing disulfonate surfactants |
| US6552107B1 (en) * | 2000-03-24 | 2003-04-22 | Council Of Scientific And Industrial Research | Melt or solution processable highly conducting polyaniline and process for preparation thereof, and blends thereof with PVC and EVA |
| US6841598B2 (en) * | 2002-08-16 | 2005-01-11 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
| CN1915969A (en) * | 2006-09-05 | 2007-02-21 | 太原理工大学 | Method for synthesizing alkyl diphenyl ether sulfonate |
| CN101503379A (en) * | 2009-03-23 | 2009-08-12 | 大庆油田有限责任公司 | Method for synthesizing cetyl diphenyl ether sodium disulfonate and use |
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| A Superior Synthesisi of Diaryl Ethers by the Use of Ultrasound in the Ullmann Reaction;Keith Smith et al;《J.Chem.Soc.Perkin Trans I》;19921231;407-408 * |
| 十二烷基二苯醚二磺酸钠的合成;苏瑜等;《精细化工》;20020831;第19卷(第8期);443-445 * |
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